CN117126168A - Bicarbazole compound composition containing para-biphenyl substituent and organic electroluminescent device containing same - Google Patents
Bicarbazole compound composition containing para-biphenyl substituent and organic electroluminescent device containing same Download PDFInfo
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- CN117126168A CN117126168A CN202311090215.2A CN202311090215A CN117126168A CN 117126168 A CN117126168 A CN 117126168A CN 202311090215 A CN202311090215 A CN 202311090215A CN 117126168 A CN117126168 A CN 117126168A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 107
- 239000000203 mixture Substances 0.000 title claims abstract description 45
- 239000004305 biphenyl Substances 0.000 title claims abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 230000000903 blocking effect Effects 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000010409 thin film Substances 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001975 deuterium Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 43
- 238000001704 evaporation Methods 0.000 description 21
- 230000008020 evaporation Effects 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000010408 film Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 238000001308 synthesis method Methods 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 125000006267 biphenyl group Chemical group 0.000 description 7
- 238000004949 mass spectrometry Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005238 degreasing Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000001046 green dye Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K50/00—Organic light-emitting devices
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- H10K50/18—Carrier blocking layers
- H10K50/181—Electron blocking layers
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
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- H10K85/649—Aromatic compounds comprising a hetero atom
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- Physics & Mathematics (AREA)
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- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a composition of a bicarbazole compound containing para-biphenyl substituent and an organic electroluminescent device containing the composition. The composition comprises a first host compound and a second host compound, wherein the first host compound has a structure shown in the following formula I, and the second host compound has a structure shown in the following formula II. The composition provided by the invention is used as a material of a luminescent layer of an organic electroluminescent device, and the prepared OLED device has lower driving voltage, higher current efficiency and longer service life.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a composition of a bicarbazole compound containing para-biphenyl substituent groups and an organic electroluminescent device containing the composition.
Background
Currently, the organic electroluminescence (OLED) display technology has been applied in the fields of smart phones, tablet computers and the like, and further will expand to the fields of large-size applications such as televisions and the like. In the development process of the last 30 years, various OLED materials with excellent performance are developed, and the commercialization process of the OLED is accelerated through different designs of device structures and optimization of the performances such as service life, efficiency and the like of the device, so that the OLED is widely applied to the display and illumination fields.
The choice of materials for the hole layer, the light-emitting layer and other organic functional layers also has a great influence on the current efficiency, the driving voltage and the lifetime of the device, and functional layer materials with higher performance are still being explored at present.
Accordingly, in order to meet the higher demands of OLED devices, there is a need in the art to develop more kinds of higher performance OLED materials.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a composition of a bicarbazole compound containing para-biphenyl substituent and an organic electroluminescent device containing the composition. In the invention, the specific composition of the composition and the structures of the first main body compound and the second main body compound are designed, and the composition is used as a material of a luminescent layer of the organic electroluminescent device, so that the prepared OLED device has lower driving voltage, higher current efficiency and longer service life.
To achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides a composition of a dicarbazole compound containing a para-biphenyl substituent, the composition comprising a first host compound having a structure according to formula I below, and a second host compound having a structure according to formula II below:
wherein Y is selected from any one of O, S,
a. h is independently selected from 0 or 5, b, d, f, g, k, l, n is independently selected from 0 or 4, c, e is independently selected from 0 or 3, m is selected from 0 or 2, i, j is independently selected from 0, 3, 4 or 5, and a-h are not 0 at the same time and i-n are not 0 at the same time;
Ar 1 、Ar 2 is absent or each independently selected from any one of deuterium atom (D), unsubstituted phenyl, unsubstituted naphthyl, fully deuterated phenyl or fully deuterated naphthyl, and Ar 1 、Ar 2 Wherein at least one is selected from any one of unsubstituted phenyl, unsubstituted naphthyl, fully deuterated phenyl or fully deuterated naphthyl, and Ar 1 、Ar 2 Each independently of the other can be linked to the benzene ring through-O-, -S-, -C (CH) 3 ) 2 -or-C (CD) 3 ) 2 -bridging.
In the invention, the specific composition of the composition and the structures of the first main body compound and the second main body compound are designed, and the composition is used as a material of a luminescent layer of the organic electroluminescent device, so that the prepared OLED device has lower driving voltage, higher current efficiency and longer service life.
In the invention, the structure of the first main body compound is designed to contain two biphenyl groups, one biphenyl group is selected as a para biphenyl group, and if the other biphenyl group is an ortho biphenyl group or a meta biphenyl group, the composition has better film forming property, so that the prepared organic electroluminescent device has longer service life; if the other biphenyl group is also para-biphenyl group, the driving voltage of the organic electroluminescent device can be further reduced, and the current efficiency of the organic electroluminescent device can be improved.
The composition is more suitable for being used as a main material of a luminescent layer of a phosphorescent green device through the design of the structure of the second main compound.
In the structures shown in the above formulas I and II, D is a deuterium atom (the same applies hereinafter).
The following is a preferred technical scheme of the present invention, but not a limitation of the technical scheme provided by the present invention, and the following preferred technical scheme can better achieve and achieve the objects and advantages of the present invention.
As a preferred technical scheme of the invention, the first main compound has a structure shown as the following formula I-1 or formula I-2:
as a preferable embodiment of the present invention, the first host compound is selected from any one of the compounds H-1 to H-6:
in a preferred embodiment of the present invention, in the second host compound, l is selected from 4, m is selected from 2, n is selected from 4, i is selected from 0, j is selected from 0, and k is selected from 0.
As a preferred technical scheme of the invention, the second main compound has a structure shown in the following formulas II-1 to II-5:
wherein X is selected from O, S.
The method for preparing the first host compound or the second host compound in the present invention is not particularly limited, and may be prepared by a method conventional in the art.
As a preferable embodiment of the present invention, the second host is selected from any one of the compounds E1 to E19:
in a second aspect, the present invention provides a compound comprising any one of the following compounds:
the compound is used for preparing the composition according to the first aspect.
In the above-mentioned compound, D is a deuterium atom (the same applies hereinafter).
The present invention provides an organic electroluminescent device including an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode;
the material of the organic thin film layer comprises the composition according to the first aspect.
Preferably, the organic thin film layer includes a light emitting layer.
The material of the light emitting layer comprises the composition according to the first aspect.
Preferably, the organic electroluminescent device is a green device.
As a preferred embodiment of the present invention, the organic thin film layer includes a hole layer.
Preferably, the hole layer comprises an electron blocking layer, and the material of the electron blocking layer comprises a spirofluorene compound;
the spirofluorene compound has a structure shown in a formula III:
wherein X is selected from O or S;
R 11 、R 21 each independently selected from hydrogen, deuterium, fluorine, CN, substituted or unsubstituted C1 to C20 (e.g., may be C1, C2, C3, C4, C5, C7, C8, C9, C10, C13, C15, C18, or C20, etc.) linear or branched alkyl, substituted or unsubstituted C1 to C20 (e.g., may be C1, C2, C3, C4, C5, C7, C8, C9, C10, C13, C15, C18, or C20, etc.) alkoxy, substituted or unsubstituted C6 to C40 (e.g., may be C6, C8, C10, C12, C15, C18, C24, C30, C36, or C40, etc.) aryl;
ar is selected from substituted or unsubstituted C6-C40 (e.g., C6, C8, C10, C12, C15, C18, C24, C30, C36, C40, etc.) arylene;
Ar 1 、Ar 2 each independently selected from substituted or unsubstituted C6-C40 (e.g., may be C6, C8, C10, C12, C15, C18, C24, C30, C36, or C40, etc.) aryl, substituted or unsubstituted C12-C40 (C12, C14, C16, C18, C20, C23, C25, C27, C30, C32, C35, C37, C39, or C40, etc.) oxaheteroaryl, substituted or unsubstituted C12-C40 (C12, C14, C16, C18, C20, C23, C25, C27, C30, C32, C35, C37, C39, or C40, etc.) thiaheteroaryl, and at least one of Ar1 or Ar2 is selected from any of phenyl, naphthyl, triphenylenyl, or fluoranthenyl; p is pSelected from 0 or 1;
m and n are each independently selected from integers of 0 to 4, and may be, for example, 0, 1, 2, 3, or 4.
The oxaheteroaryl group is a structure formed by bridging two aromatic rings connected by a single bond through an O atom and having an oxygen-containing five-membered heterocyclic ring, for example, two benzene rings are connected by a single bond to form biphenyl, and carbon atoms on the two benzene rings forming the biphenyl are simultaneously connected with the O atom to form dibenzofuran.
The thiaheteroaryl refers to a structure with sulfur-containing five-membered heterocyclic ring formed by bridging two aromatic rings connected by a single bond through an S atom, for example, two benzene rings are connected into biphenyl by a single bond, and carbon atoms on the two benzene rings forming the biphenyl are simultaneously connected with the S atom to form dibenzothiophene.
Preferably, the spirofluorene compound is selected from the group consisting of a compound represented by III-1 and a compound represented by III-2:
therein, X, X 1 Each independently selected from O or S;
R 11 、R 21 ar has the same protection scope as described above;
Ar 1 any one selected from phenyl, naphthyl, triphenylene or fluoranthenyl;
R 31 selected from C1-C20 (e.g., C1, C2, C3, C4, C5, C7, C8, C9, C10, C13, C15, C18, or C20, etc.) linear or branched alkyl, C1-C20 (e.g., C1, C2, C3, C4, C5, C7, C8, C9, C10, C13, C15, C18, or C20, etc.) alkoxy, C6-C40 (e.g., C6, C8, C10, C12, C15, C18, C24, C30, C36, or C40, etc.) aryl;
R 41 、R 42 each independently selected from C1-C20 (exampleFor example, it may be C1, C2, C3, C4, C5, C7, C8, C9, C10, C13, C15, C18 or C20, etc.), a linear or branched alkyl group, a C6 to C40 (for example, it may be C6, C8, C10, C12, C15, C18, C24, C30, C36 or C40, etc.) aryl group, and R 41 And R is 42 Independent of each other or linked by a single bond to form a ring.
Preferably, the spirofluorene compound is selected from any one of the following compounds 1-140 and compounds 1S-140S:
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the compound 1S-140S is obtained by combining the compounds 1-140Replaced by->Wherein the dotted line indicates the ligation site.
The structure of the compound 2 isThe structure of compound 2S is: />
Preferably, the electron blocking layer compound is selected from the group consisting of compounds EB-D and EB-E:
more preferably, the electron blocking material is selected from compounds EB-E.
In a fourth aspect, the present invention provides a display device comprising an organic electroluminescent device as described in the third aspect.
Compared with the prior art, the invention has the following beneficial effects:
in the present invention, by designing the specific composition of the composition and the structures of the first host compound and the second host compound, a composition having a specific composition is further obtained by selecting at least one of the two biphenyl groups in the first host compound to be a para-biphenyl group and defining the structure of the second host compound. The OLED device prepared by using the composition as the material of the luminous layer of the organic electroluminescent device has lower driving voltage, higher current efficiency and longer service life.
Detailed Description
To facilitate understanding of the present invention, examples are set forth below. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
Synthesis example 1
This example provides compound E1 and a method of synthesis thereof, as follows:
into a 250L three-necked flask, 100L of dried toluene, intermediate E1-M1 (0.01 mol), intermediate E1-M2 (0.11 mol), pd (dba) were charged under nitrogen 2 (bis (dibenzylidene) palladium acetonate, 0.0575 g), a toluene solution of tri (t-butylphosphine) having a mass percent of 10% (the mass of the tri (t-butylphosphine) solution is 0.8g, the mass of the tri (t-butylphosphine) is 0.0004 mol) and sodium t-butoxide (1.44 g), heating to reflux for 8 hours, cooling to room temperature, adding water to the aqueous solution, washing the organic layer with water to neutrality, drying over magnesium sulfate, filtering to remove magnesium sulfate, concentrating to dryness, crystallizing the mixed solvent of toluene and chloroform to give compound E1 (4.7 g)
Mass spectrometry detection of compound E1: the mass to charge ratio (m/z) was measured to be 650.29.
Synthesis example 2
This example provides compound E2 and a method of synthesis thereof, as follows:
referring to the synthesis method of E1, E2 is prepared.
The obtained E2 was subjected to mass spectrometry, and the mass-to-charge ratio (m/z) was 666.27.
Synthesis example 3
This example provides compound E3 and a method of synthesis thereof, as follows:
300mL of toluene, 90mL of ethanol and 50mL of water are sequentially added into a 1000mL three-necked flask under the protection of nitrogen, 0.01mol of intermediate E3-M1, 0.01mol of intermediate E3-M2, 2.12g (0.02 mol) of sodium carbonate and 0.23g (0.0002 mol) of tetraphenylphosphine palladium are added, the temperature is slowly increased to 100 ℃ for reaction for 6 hours, the temperature is reduced to room temperature, water is added, the organic layer is washed by water, then dried by magnesium sulfate, the drying agent is removed, and then the mixture is concentrated to dryness for silica gel column chromatography separation, and petroleum ether is ethyl acetate: dichloromethane = 20:1:1 (volume ratio) to give 5.5g of compound E3.
Mass spectrometry was performed on the obtained compound E3 to determine that the mass-to-charge ratio (m/z) was 650.29
Synthesis examples 4 to 19
Examples 4-19 provide a compound and a synthesis method thereof, respectively, wherein the corresponding compound is obtained by reacting and synthesizing the reactant 1 and the reactant 2, the synthesis method is referred to the synthesis method provided in synthetic example 3, and the specific reactant and the structure of the prepared compound are shown in table 1.
Mass spectrometry was performed on the synthesized compounds, and mass to charge ratios (m/z) are shown in Table 1.
TABLE 1
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Other compounds not specifically identified as synthetic steps may be prepared by the general knowledge in the art, in combination with the above examples.
Preparation example 1
The preparation example provides an intermediate M1D and a synthesis method thereof, wherein the synthesis method comprises the following steps:
into a 500mL autoclave were charged 0.01mol of raw material M1, palladium acetate (0.02 g), activated carbon (0.2 g), D at room temperature 2 O (26 mL) and C 6 D 6 (100 mL), introducing hydrogen to the pressure of 0.02MPa, then heating to 90 ℃ for reaction for 110 hours, cooling to room temperature, filtering, separating liquid, drying the separated organic layer by magnesium sulfate, decolorizing by a short silica gel column, concentrating to dryness, and recrystallizing by ethanol to obtain 2.38 g of intermediate shown as M1D.
Mass spectrometry was performed on the obtained intermediate M1D, and the mass-to-charge ratio (M/z) was measured to be 268.15.
Preparation example 2
The preparation example provides an intermediate M2D and a synthesis method thereof, wherein the synthesis method comprises the following steps:
referring to the preparation method of M1D, 2.21 g of intermediate shown in M2D is prepared.
Mass spectrometry was performed on the obtained intermediate M2D, and the mass-to-charge ratio (M/z) was 268.15.
Performing hydrogen spectrum nuclear magnetic analysis on the obtained intermediate M2D to obtain 1 H-NMR (Bruker, switzerland, avance II 400MHz Nuclear magnetic resonance spectrometer, CDCl) 3 ) No H peak.
Synthesis of the compounds DE-2, DE-3, DE-4, DE-5, DE-6
The corresponding compound is obtained by the reaction and synthesis reaction of the reactant 1 and the reactant 2, the synthesis method is referred to as the synthesis method provided in synthesis example 1, and the specific reactant and the structure of the prepared compound are shown in table 2.
Mass spectrometry was performed on the synthesized compounds, and mass to charge ratios (m/z) are shown in Table 2.
TABLE 2
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The specific structures of the compounds used in the following device application examples and device comparative examples are as follows:
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device application example 1
Application example 1 of the device provides an organic electroluminescent device, and the composition provided by the invention is selected as a green light main body material in the organic electroluminescent device.
The structure of the organic electroluminescent device is as follows: ITO/HT-1 (20 nm)/green host material (35 nm): ir (ppy) 3[10% ]/TPBI (10 nm)/Alq 3 (15 nm)/LiF (0.5 nm)/Al (150 nm). Wherein "Ir (ppy) 3[10% ]" means a doping ratio of the green dye, i.e., a volume part ratio of the green host material to Ir (ppy) 3 is 90:10.
The preparation process of the organic electroluminescent device comprises the following steps:
(1) The glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;
(2) Placing the above glass substrate with anode in vacuum chamber, and vacuumizing to 1×10 -5 ～9×10 -4 Pa, vacuum evaporating a hole transport layer HT-1 on the anode layer film, wherein the evaporation rate is 0.1nm/s, and the thickness of the evaporation film is 20nm;
(3) Vacuum evaporating green light host material and dye Ir (ppy) 3 on the hole transport layer to obtain a luminescent layer of the organic electroluminescent device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 35nm; in the application example of the device, the first main body compound H-1 and the second main body compound E3 are respectively placed in different evaporation sources for heating, and the heating speed is controlled so that the volume ratio of the first main body compound H-1 and the second main body compound E3 to the substrate is 1:1, and the green main body material is obtained.
(4) Sequentially carrying out vacuum evaporation on the electron transport layers TPBI and Alq3 on the luminescent layer, wherein the evaporation rates are 0.1nm/s, and the evaporation film thicknesses are respectively 10nm and 15nm;
(5) LiF of 0.5nm and Al of 150nm are vacuum evaporated on the electron transport layer as an electron injection layer and a cathode.
Device application examples 2 to 14
The device application examples 2 to 14 respectively provide an organic electroluminescent device, which is different from the device application example 1 only in that the green host material is different, the specific selection of the green host material is shown in table 3, the volume ratio of the two components in the green host material to the substrate by vapor deposition is 1:1, and other preparation steps and conditions are the same as the device application example 1.
Device application comparative examples 1 to 5
Device application comparative examples 1 to 5 respectively provide an organic electroluminescent device differing from device application example 1 only in that the first host compound and/or the second host compound in the green host material are different, specific choices of the green host material are shown in table 3, the volume ratio of the two components in the green host material evaporated onto the substrate is 1:1, and other preparation steps and conditions are the same as those of device application example 1.
Performance test:
the brightness, driving voltage, current efficiency and service life test LT90 of the prepared organic electroluminescent device are measured by using an OLED-1000 multichannel accelerated aging service life and photochromic performance analysis system test produced by Hangzhou remote production. Wherein, the life test LT90 means that the current density at the initial luminance is kept constant at room temperature (25 to 27 ℃ C.) (here, 1000 cd/m) 2 ) The time required for the luminance to decrease to 90% of the initial luminance. In the following table, the driving voltage, current efficiency, LT90 lifetime are all relative values, and the test results are shown in table 3 below.
TABLE 3 Table 3
As can be seen from the contents of table 2, by designing specific compositions of the compositions and structures of the first host compound and the second host compound, compositions having specific compositions were obtained. The OLED device prepared by using the composition as the material of the luminous layer of the organic electroluminescent device has lower driving voltage, higher current efficiency and longer service life.
As is clear from the device application examples 1, 2 and 3, in the second host compound, when l is selected from 4, m is selected from 2, n is selected from 4, i is selected from 0, j is selected from 0, and k is selected from 0, the lifetime of the device is slightly reduced, but the device voltage and efficiency are superior, and in this case, the second compound has fewer D atoms, so that the material cost can be suitably reduced. Therefore, the comprehensive performance is better.
As is clear from device application example 7, when the second host compound is selected from E11, the device voltage decreases.
From the device application examples 10 and 11, it is understood that the second host compound does not have Ar1 or Ar2, and that the device lifetime is good when the other compound is selected from naphthyl. And when Y is selected from S, the device lifetime is further improved.
As is clear from the device application examples 1 and 12, the device voltage and efficiency were good when the first host compound contained two para-biphenyl groups. When containing a para-biphenyl group, the device lifetime is better.
As is clear from the device application examples 12 and 14, the device comprehensive performance is excellent when a, b, g, h, and f are selected from 0, d, and f, and c, respectively, and e, are selected from 3, respectively, in the first host compound.
Device application example 15
The application example of the device provides an organic electroluminescent device, and the composition provided by the invention is selected as a green light main body material in the organic electroluminescent device.
The structure of the organic electroluminescent device is as follows: ITO/HT-1 (20 nm)/electron blocking layer (5 nm)/green host material (35 nm): ir (ppy) 3[10% ]/TPBI (10 nm)/Alq 3 (15 nm)/LiF (0.5 nm)/Al (150 nm). Wherein "Ir (ppy) 3[10% ]" means a doping ratio of the green dye, i.e., a volume part ratio of the green host material to Ir (ppy) 3 is 90:10.
The preparation process of the organic electroluminescent device comprises the following steps:
(1) The glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;
(2) Placing the above glass substrate with anode in vacuum chamber, and vacuumizing to 1×10 -5 ～9×10 -4 Pa, vacuum evaporating a hole transport layer HT-1 on the anode layer film, wherein the evaporation rate is 0.1nm/s, and the thickness of the evaporation film is 20nm;
(3) Vacuum evaporation EB is used as an electron blocking layer on the hole transport layer, the evaporation rate is 0.1nm/s, and the thickness of the evaporation film is 5nm;
(4) Vacuum evaporating green light host material and dye Ir (ppy) 3 on the electron blocking layer to obtain a luminescent layer of the organic electroluminescent device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 35nm; in this embodiment, the first host compound H-1 and the second host compound E1 are respectively placed in different evaporation sources for heating, and the heating speed is controlled so that the volume ratio of the two to the substrate by evaporation is 1:1, and the green host material is obtained.
(5) Sequentially carrying out vacuum evaporation on the electron transport layers TPBI and Alq3 on the luminescent layer, wherein the evaporation rates are 0.1nm/s, and the evaporation film thicknesses are respectively 10nm and 15nm;
(6) LiF of 0.5nm and Al of 150nm are vacuum evaporated on the electron transport layer as an electron injection layer and a cathode.
Device application examples 16 to 17
Device application examples 16 to 17 provided an organic electroluminescent device differing from device application example 15 only in the electron blocking layer material (see table 4 below for details), and the other preparation steps and conditions were the same as those of device application example 15.
Performance test:
the brightness, driving voltage, current efficiency and service life test LT90 of the prepared organic electroluminescent device are measured by using an OLED-1000 multichannel accelerated aging service life and photochromic performance analysis system test produced by Hangzhou remote production. Wherein, the life test LT90 means that the current density at the initial luminance is kept constant at room temperature (25 to 27 ℃ C.) (here, 1000 cd/m) 2 ) The time required for the luminance to decrease to 90% of the initial luminance. In the following table, the driving voltage, current efficiency, LT90 lifetime are all relative values, and the test results are shown in table 4 below.
TABLE 4 Table 4
As can be seen from the contents of table 4, the organic electroluminescent device prepared by selecting the spirofluorene compound with a specific structure as the electron blocking layer material and combining the composition comprising the first host compound and the second host compound as the light emitting layer material in the present invention has higher current efficiency and longer service life.
The device star can be further improved, especially when the electron blocking layer is selected from EB-E.
The applicant states that the detailed process flow of the present invention is illustrated by the above examples, but the present invention is not limited to the above detailed process flow, i.e. it does not mean that the present invention must be implemented depending on the above detailed process flow. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.
Claims (10)
1. A composition of a bicarbazole compound containing a para-biphenyl substituent, which is characterized by comprising a first main compound and a second main compound, wherein the first main compound has a structure shown in the following formula I, and the second main compound has a structure shown in the following formula II:
wherein Y is selected from any one of O, S,
a. h is independently selected from 0 or 5, b, d, f, g, k, l, n is independently selected from 0 or 4, c, e is independently selected from 0 or 3, m is selected from 0 or 2, i, j is independently selected from 0, 3, 4 or 5, and a-h are not 0 at the same time and i-n are not 0 at the same time;
Ar 1 、Ar 2 is absent or each independently selected from any one of deuterium atom, unsubstituted phenyl, unsubstituted naphthyl, fully deuterated phenyl or fully deuterated naphthyl, and Ar 1 、Ar 2 Wherein at least one is selected from any one of unsubstituted phenyl, unsubstituted naphthyl, fully deuterated phenyl or fully deuterated naphthyl, and Ar 1 、Ar 2 Each independently of the other can be linked to the benzene ring through-O-, -S-, -C (CH) 3 ) 2 -or-C (CD) 3 ) 2 -bridging.
2. The composition of claim 1, wherein the first host compound has a structure according to formula I-1 or formula I-2:
3. the composition according to claim 1 or 2, wherein the first host compound is selected from any one of compounds H-1 to H-6:
4. a composition according to any one of claims 1 to 3, wherein in the second host compound, i is selected from 4, m is selected from 2, n is selected from 4, i is selected from 0, j is selected from 0, k is selected from 0;
preferably, the second host compound has a structure represented by the following formulas II-1 to II-5:
wherein X is selected from O, S.
5. The composition according to any one of claims 1-4, wherein the second host is selected from any one of compounds E1-E19:
6. a compound, characterized in that the compound comprises any one of the following compounds:
the compound is used for preparing the composition as claimed in any one of claims 1 to 5.
7. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode;
the material of the organic thin film layer comprising the composition of any one of claims 1 to 5;
preferably, the organic thin film layer includes a light emitting layer;
a material of the light emitting layer comprising the composition of any one of claims 1 to 5;
preferably, the organic electroluminescent device is a green device.
8. The organic electroluminescent device according to claim 7, wherein the organic thin film layer comprises a hole layer;
preferably, the hole layer comprises an electron blocking layer, and the material of the electron blocking layer comprises a spirofluorene compound;
the spirofluorene compound has a structure shown in a formula III:
wherein X is selected from O or S;
R 11 、R 21 each independently selected from hydrogen, deuterium, fluorine, CN, substituted or unsubstituted C1 to C20 straight or branched alkyl, substituted or unsubstituted C1 to C20 alkoxy, substituted or unsubstituted C6 to C40 aryl;
ar is selected from substituted or unsubstituted C6-C40 arylene;
Ar 1 、Ar 2 each independently selected from the group consisting of substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C12-C40 oxaheteroaryl, substituted or unsubstituted C12-C40 thiaheteroaryl, and Ar 1 Or Ar 2 At least one of the groups is selected from any one of phenyl, naphthyl, triphenylene or fluoranthenyl;
p is selected from 0 or 1;
m and n are each independently selected from integers of 0 to 4.
9. The organic electroluminescent device of claim 8, wherein the electron blocking layer compound is selected from the group consisting of compound EB-D and compound EB-E:
preferably, the electron blocking layer compound is selected from compounds EB-E.
10. A display device, characterized in that it comprises an organic electroluminescent device as claimed in any one of claims 7-9.
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